Dimethyl Phthalate → HCID 178509848, compound

HRID 365472

Reaction equation

HRID 365472 reaction equation
[Br-].C(OC[N+:10]1[CH:14]=[C:13]([CH2:15][CH2:16][N:17]2C(=O)C3=CC=CC=C3[C:18]2=O)[N:12](CC2C=CC(C#N)=CC=2)[CH:11]=1)(=O)C(C)(C)C.[NH2:37]N.C(OC)(=O)[C:40]1[C:41](=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:42](OC)=O>C(O)C>[C:42]([C:41]1[CH:40]=[CH:49][C:48]([CH2:18][NH:17][CH2:16][CH2:15][C:13]2[N:12]=[CH:11][NH:10][CH:14]=2)=[CH:47][CH:46]=1)#[N:37]

Participants

5

Reactant 3

HCID 8554Dimethyl PhthalateHCID 9321HydrazineHCID 86755883HCID 86755883, compound

Product 1

HCID 178509848HCID 178509848, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Pivaloyloxymethyl-3-(4-cyanobenzyl)-4-(2-phthalimidoethyl) imidazolium bromide (1.00 g, 1.81 mmol) was dissolved in ethanol (50 mL), treated with hydrazine (0.287 mL, 9.06 mmol), and heated at reflux for 16 h. Dimethyl phthalate (2.22 mL, 13.57 mmol) was added and reflux was continued for 6 h. The reaction mixture was cooled in an ice-H2O bath, the solid precipitate filtered off, the filtrate concentrated to dryness, and the residue chromatographed (SiO2, CH2Cl2 (NH4OH): 3-8% CH3OH) to give the title compound. 1H NMR (CD3OD) δ 7.76 (s, 1H), 7.74 (d, 2H, J=8 Hz), 7.27 (d, 2H, J=8 Hz), 6.88 (s, 1H), 5.35 (s, 2H), 2.76 (t, 2H, J=6 Hz), 2.60 (t, 2 H, J=6 Hz).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. temperaturereflux
  4. temperatureThe reaction mixture was cooled in an ice-H2O bath
  5. filtrationthe solid precipitate filtered off
  6. concentrationthe filtrate concentrated to dryness
  7. customthe residue chromatographed (SiO2, CH2Cl2 (NH4OH): 3-8% CH3OH)

Sources & evidence

ORD record
ord-3bd4b4962be24736b720693d111001fd
Source dataset
uspto-grants-2000_10
Patent number
US06127390

Linked notes

Loading…